About 209 Main Street
Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and carefully selected reproduction details creating warmth and authenticity. Multiple living and dining spaces unfold effortlessly, anchored by six fireplaces, including an impressive 12' natural stone Rumford. With seven spacious bedrooms-each with its own private bath-the home is uniquely suited for multi-generational living, hosting, or continued hospitality use. The third-floor suite offers a private retreat with a wood-burning fireplace, perfect for extended family or guests. A new kitchen addition further enhances flexibility, easily accommodating in-law living or private guest quarters. Curated perennial gardens, a white oak pergola, and a beautifully crafted stone terrace create a setting designed for gathering and relaxation. Enjoy evenings by the fire pit, surrounded by timeless landscape design. This property offers style, comfort and charm all amidst the local shops, restaurants, marinas, and nearby shoreline destinations-all within two hours of both NY and Boston. Previously, an Award-Winning Bed & Breakfast, and currently featuring two Airbnb guest suites with private access.
Features of 209 Main Street
| MLS® # | 24179935 |
|---|---|
| Price | $1,199,999 |
| Bedrooms | 9 |
| Bathrooms | 9.00 |
| Full Baths | 9 |
| Square Footage | 4,982 |
| Acres | 0.45 |
| Type | Single Family For Sale |
| Style | Colonial, Antique |
| Status | Active |
Community Information
| Address | 209 Main Street |
|---|---|
| Area | N/A |
| City | Deep River |
| County | Middlesex |
| State | Connecticut |
| Zip Code | 06417 |
Amenities
| Parking Spaces | 10 |
|---|---|
| Parking | Driveway |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | No |
Interior
| Appliances | Electric Cooktop, Gas Range, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer |
|---|---|
| Heating | Hot Water, Natural Gas, Oil |
| Cooling | Split System, Window Unit |
| Fireplace | Yes |
| # of Fireplaces | 6 |
| Has Basement | Yes |
| Basement | Full, Storage, Interior Access, Concrete Floor, Full With Hatchway |
Exterior
| Exterior | Clapboard |
|---|---|
| Exterior Features | Porch-Wrap Around, Sidewalk, Shed, Porch, Wrap Around Deck, Gutters, Garden Area, Patio |
| Lot Description | Level Lot, Professionally Landscaped |
| Roof | Asphalt Shingle |
| Foundation | Concrete, Stone |
School Information
| Elementary | Deep River |
|---|---|
| Middle | Per Board of Ed |
| High | Per Board of Ed |
Additional Information
| Date Listed | June 1st, 2026 |
|---|---|
| Days on Market | 100 |
| Zoning | VCD |
| RE / Bank Owned | No |
Listing Details
| Office | William Pitt Sotheby's Int'l |
|---|